Note: Descriptions are shown in the official language in which they were submitted.
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AQUEOUS DISPERSIBLE STERYL ESTER COMPOSITIONS
TECHNICAL FIELD
The present invention relates to the formulation and delivery of steryl
esters.
More specifically, it relates to water dispersible formulations of steryl
esters.
BACKGROUND
Coronary heart disease (CHD) is a common and serious form of cardiovascular
disease that causes more deaths in the U.S. every year than any other disease.
High
serum cholesterol, and especially high levels of low density lipoprotein (LDL)
o cholesterol, are risk factors associated with CHD. Research has shown that
esters of plant
sterols or stanols (i.e., steryl esters) may lower total and LDL cholesterol
and thereby
reduce the risk of CHD.
One way that individuals can get more esters of sterols or stanols into their
diets is
by consuming fortified or "functional" foods. The FDA has authorized use of
labeling
15 health claims about the role of such esters in reducing the risk of
coronary heart disease
(CHD) for specific foods containing these substances. It advises that foods
containing at
least 0.65 g per serving of plant sterol esters, eaten twice a day with meals
for a daily total
intake of at least 1.3 g (or 1.7g of stanol esters twice a day for a total of
3.4g), as part of a
diet low in saturated fat and cholesterol, may reduce the risk of heart
disease.
2o Because steryl esters are fat soluble, hydrophobic ingredients, they
typically have
been utilized in fat based foods such as margarines, spreads, salad dressings,
and
mayonnaise. While this approach is a technical solution to formulating with
these
ingredients, it is contradictory and confusing to cholesterol-conscious
consumers who are
trying to reduce the amount of fat in their diets.
25 There is a need for technology to allow use of steryl esters in aqueous
systems to
facilitate healthier food choices. Further, the development of water
dispersible steryl
esters will increase the variety of foods consumers may choose from to achieve
their
twice daily servings of such esters.
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SUMMARY
The present invention is based on the discovery of formulations that allow
steryl
esters to be easily incorporated into aqueous foods and beverages and that are
able to
withstand conditions of heat, acid, and water hardness. Such compositions are
powders
or low viscosity, water-soluble fluids that are easily stirred into beverages
or other non-fat
foods. The compositions leave a clean mouthfeel without the waxy or
mouthcoating
characteristics that can be associated with sterols, stanols, steryl ester,
and stanol ester
fortified foods.
The compositions are complex oil-in-water emulsions that can be formulated to
be
bland, flavored, or sweetened. Advantageously, providing steryl esters in the
form of the
emulsified compositions improves the handling properties of the steryl esters.
While
steryl esters themselves are viscous, sticky, and difficult to measure and
clean up,
emulsions of steryl esters are very fluid (or powdered), easy to pump and
measure, and
readily water dispersible, properties that make handling and clean-up easier.
Any of the individual elements of the present invention may be comprised of
mixtures of components that serve the function indicated. For example the
protein
identified in the claims of the present invention may be, but need not be,
comprised of a
mixture of protein components.
In one aspect, the invention features a composition that includes the
following
2o ingredients: 1 to 75 weight % (wt %) of a steryl ester; 0.3 to 10 wt % of a
protein (e.g., a
caseinate or sodium, calcium, or potassium caseinate salt); 0.1 to 5 wt % of
an emulsifier
(e.g., 0.1 to 2 wt %); 0.1 to 5 wt % of a buffer (e.g., dipotassium
phosphate); and 0 to 98.5
wt % of a liquid. The protein can be present at 2 to 3 wt % of the
composition. The
composition further can include one or more additional components selected
from the
group consisting of bulking agents, thickeners, and fats and/or one or more
additional
components selected from the group consisting of flavorings, coloring agents,
sweeteners,
antioxidants, and flow agents. The fatty acid moiety of the steryl ester can
be a blend of
C16 to C18 carbon chains. The invention also features food compositions
containing
such steryl ester compositions (e.g., 0.5 to 60 wt % of such a steryl ester
composition).
3o In some embodiments, the steryl ester can be 1 to 40 wt % of the
composition and
the liquid can be 20 to 98 wt % of the composition. In other embodiments, the
steryl ester
2
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can be 1 to 7S wt % of the composition and the liquid can be 0 to S wt % of
the
composition.
A composition can include 1 to 10 wt % of a steryl ester; O.S to 1.S wt % of a
protein; 0.2 to 0.6 wt % of an emulsifier; 0.1 to 1.S wt % of a buffer; O.S to
1S wt % of a
s bulking agent; 3 to 10 wt % of a fat; and 40 to 80 wt % of a liquid. In such
a
composition, the protein can be a caseinate, the emulsifier can include mono-
and
diglycerides or esters thereof, the buffer can be dipotassium phosphate, the
bulking agent
can be corn syrup solids, the fat can be a partially hydrogenated vegetable
oil, and the
liquid can be water.
o In other embodiments, a composition includes 1S to 2S wt % of a steryl
ester; O.S
to 8 wt % of a protein; 0.2 to 1 wt % of an emulsifier; 0.1 to 1.S wt % of a
buffer; O.S to
3S wt % of a bulking agent; 0 to 4 wt % of a fat; and 3S to 80 wt % of a
liquid. The
invention also features food compositions containing such steryl ester
compositions (e.g.,
1 to 40 wt % of such a steryl ester composition).
15 A composition also can include about S to 1 S wt % of a steryl ester, 1 to
S wt % of
a protein, 0.3 to 1.S wt % of an emulsifier; 1 to 3 wt % of a buffer, 70 to 80
wt % of a
bulking agent, and S to 10 wt % of a fat. The protein can be a caseinate, the
emulsifier
can include mono- and diglycerides or esters thereof, the buffer can be
dipotassium
phosphate, the bulking agent can be corn syrup solids, and the fat can be a
partially
2o hydrogenated vegetable oil. A food composition can include 20 to 40 wt % of
such
compositions.
In another aspect, the invention features a method of making an aqueous
dispersible steryl ester composition, where the composition includes 1 to 7S
wt % of a
steryl ester, 0.3 to 10 wt % of a protein, 0.1 to S wt % of an emulsifier; 0.1
to S wt % of a
25 buffer, and 0 to 98.5 wt % of a liquid. The method can include combining
the steryl ester
and emulsifier under conditions suitable to form a melt; combining the melt
with the
protein, wherein the protein is in an aqueous phase, to form an emulsion; and
homogenizing the emulsion. The method further can include drying the emulsion
to form
a powdered product.
so In yet another aspect, the invention features a composition that includes
the
following ingredients: 1 to 7S wt % of a steryl ester; 0.3 to 1 S wt % of
octenylsuccinate
3
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anhydride starch (OSAN/n-OSAI~ (e.g., 1 to 3 wt %); 0.1 to 5 wt % of an
emulsifier
(e.g., 0.1 to 2 wt %); and 0 to 98.6 wt % of a liquid. Such a composition
further can
include one or more additional components selected from the group consisting
of buffers,
bulking agents, thickeners, and fats and/or one or more additional components
selected
from the group consisting of flavorings, coloring agents, sweeteners,
antioxidants, and
flow agents. The fatty acid moiety of the steryl ester can be a blend of C16
to C18 carbon
chains. The steryl ester can be 1 to 40 wt % of the composition and the liquid
can be 20
to 98 wt % of the composition. A composition also can include 1 to 75 wt % of
a steryl
ester 0 to 5 wt % of a liquid. The invention also features food compositions
that include
o such steryl ester compositions (e.g., 0.5 to 60 wt %).
A composition can include 1 to 10 wt % of a steryl ester; 0.5 to 1.5 wt % of
octenylsuccinate anhydride starch; 0.2 to 0.6 wt % of an emulsifier; O.S to 15
wt % of a
bulking agent; 3 to 10 wt % of a fat; and 40 to 80 wt % of a liquid. The
emulsifier can
include mono- and diglycerides or esters thereof, the bulking agent ca~.i be
corn syrup
~ 5 solids, the fat can be a partially hydrogenated vegetable oil, and the
liquid can be water.
A composition also can include IS to 25 wt % of a steryl ester; 0.5 to 8 wt %
of
octenylsuccinate anhydride starch; 0.2 to 1 wt % of an emulsifier; 0.1 to 1.5
wt % of a
buffer; 0.5 to 35 wt % of a bulking agent; 0 to 4 wt % of a fat; and 35 to 80
wt % of a
liquid.
2o The invention also features a method of making an aqueous dispersible
steryl ester
composition. The composition includes 1 to 75 wt % of a steryl ester, 0.3 to
I5 wt % of
octenylsuccinate anhydride starch, 0.1 to 5 wt % of an emulsifier; and 0 to
98.6 wt % of a
liquid. The method includes combining the steryl ester and the emulsifier
under
conditions suitable to form a melt; combining the melt with the
octenylsuccinate
25 anhydride starch, wherein the starch is in an aqueous phase, to form an
emulsion; and
homogenizing the emulsion. The method further can include drying the emulsion
to form
a powdered product.
Unless otherwise defined, all technical and scientific terms used herein have
the
same meaning as commonly understood by one of ordinary skill in the art to
which this
3o invention pertains. Although methods and materials similar or equivalent to
those
described herein can be used in the practice or testing of the present
invention, suitable
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methods and materials are described below. All publications, patent
applications, patents,
and other references mentioned herein are incorporated by reference in their
entirety. In
case of conflict, the present specification, including definitions, will
control. In addition,
the materials, methods, and examples are illustrative only and not intended to
be limiting.
Other features and advantages of the invention will be apparent from the
following detailed description, and from the claims.
DETAILED DESCRTPTION
The invention features compositions that can be used to incorporate steryl
esters
into aqueous foods and beverages. Such compositions also are referred to as
"premixes"
o throughout the application. In general, the premixes are complex oil-in-
water emulsions
that contain steryl esters and two types of emulsifiers, a protein or a
lipophilic starch
emulsifier (both referred to herein as a stabilizer) and a second, non-protein
or non-starch
emulsifier. Premixes also can include one or more of the following: buffers,
bulking
agents, thickeners, fats, flavorings, coloring agents, sweeteners, flow
agents, and
antioxidants. Compositions of the invention can be readily dispersed in a
number of food
products, including both cold, acidic beverages such as orange juice
(especially when a
lipophilic starch is used) and hot aqueous beverages such as tea and coffee.
The
versatility of the compositions can help consumers achieve their daily level
of steryl
esters via a simple cup of coffee or any number of other foods or beverages.
Ste~yl Ester
The term "steryl ester" as used herein means the fatty acid esters of specific
plant
phytosterols such as: sitosterol, campesterol, stigmasterol, brassicasterol,
avenasterols,
and diosgenin, or mixtures of specific sterols. The specific sterols or
mixtures of sterols
may be isolated from the following sources: oilseeds such as soybeans, canola
seed, corn,
sunflower, cottonseed, palm kernel, corn fiber, soy germ, shea nut, or peanut;
tree sources
such as tall oil (from pine trees), tall oil soap or tall oiI pitch; other
plant sources such as
Mexican yam, olives, or sugar cane. In oilseeds, the most abundant
phytosterols are
sitosterol (~52 to 89% of total sterols), campesterol (~2 to 30% of total
sterols), and
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stigmasterol (up to 26% of total sterols). The chemical structures of
sitosterol,
campesterol, and stigmasterol are provided below in formulas I and II.
R=CHI, Campesterol
R=CiHs, Sitosterol
Stigmaslerol
Formula II
Also included within the definition of steryl esters axe the esterified and
hydrogenated forms of the above mentioned sterols (known in the art as
stanols)
including but not limited to sitostanol and campestanol. Further included
within this
definition are sterol ester derivatives such as ferulate esters, or succinate
esters.
The fatty acid moiety of the steryl esters can have a carbon chain ranging
from
about 8 to about 20, with carbon chains of 16 to 18 being particularly useful.
Blends of
fatty acid moieties having C16 to C18 carbon chains can be isolated from
vegetable oils,
and in particular, from high oleic acid canola oil, high oleic soybean oil,
and high oleic
stmflower oil. Suitable canola oils are described, for example, in U.S. Patent
Nos.
5,861,187, 5,850,026, and 5,840,946. In addition, seeds of a canola plant line
(line
Q4275) that yield a canola oil having an oleic acid content greater them 80%
have been
deposited with the American Type Culture Collection under Accession No. 97569.
High
oleic sunflower oils having oleic acid contents of about 86% to about 92%, can
be
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obtained from A.C. Humko, Memphis, TN. U.S. Patent No. 4,627,192 describes a
suitable high oleic acid sunflower oil. Known processes can be used to obtain
fatty acids
from vegetable oils.
The steryl esters described in the present invention are commercially
available and
well know in the art. Alternatively, steryl esters can be produced from
phytosterols,
which are typically recovered from deodorizer distillate produced during
deodorization or
refining of vegetable oils. Individual, purified phytosterols, e.g., purified
sitosterol or
purified stigmasterol, are available commercially, as are blends of sterols,
e.g., soy sterol
containing (3-sitosterol, stigmasterol, and campesterol and others. Sterols
can be obtained
as free sterols or as sterol glycosides, in which a sugar moiety is attached
to the hydroxyl
group of the sterol, or as sterol esters, in which the hydroxyl group is
attached to a fatty
acid.
Steryl esters can be produced by transesterification, in which the alcohol
moiety
from a fatty acid ester, e.g., a fatty acid methyl ester, is displaced by
another alcohol (in
this case, free sterol). Free sterol and a fatty acid methyl ester can be
reacted in the
presence of base catalysts such as sodium hydroxide or sodium methoxide, an
acid
catalyst such asp-toluene sulfonic acid, metals such as BBr3, Me3SiI, A1a03,
Ti(OR)4,
DMAP, and n-BuLi, K t-butoxide, and enzymes such as lipases, esterases, and a-
chymotrypsin. Preferably, the catalyst is food grade. Typically, free sterol
is mixed with
2o a molar excess of fatty acid esters (e.g., a 5 to 10% molar excess), and
the mixture is
heated until the sterols dissolve (approximately 1 I S to I40°C) before
addition of catalyst.
The reaction can be stirred and heated under vacuum until completion, during
which time
methanol produced from the reaction can be condensed and collected.
Alternatively, free
sterols and free fatty acids can be directly esterified according to the
methods described,
for example, in U.S. Patent No. 5,892, 068.
Fatty acid methyl esters can be produced by either esterifying free fatty
acids with
methanol or transesterifying triacylglycerols with methanol. Such reactions
can be
performed batch~ise or continuously. For example, batch transesterification of
triacylglycerols with methanol can be performed with an excess of methanol and
in the
so presence of a catalyst, e.g., an alkaline catalyst, under high pressure
(9000 kPa) and high
temperature 0240°C). See, Bailey's Industrial Oil & Fat Products:
General Applications,
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Vol. 5, pp. 49-53, John Wiley & Sons, Ins., New York, NY (1996). Similar
conditions
are used for continuous transesterification.
Steryl esters can be purified by solvent or aqueous extraction, bleaching and
deodorization, or other known methods. For example, purified steryl esters can
be
obtained by aqueous extraction by suspending the reaction products in aqueous
sodium
bicarbonate (e.g., 1%), filtering the suspension to obtain purified steryl
esters, and drying
the purified steryl esters. Reaction products can be bleached using
diatomaceous earth,
bleaching clay, activated carbon, silica, or combinations thereof. Purity of
steryl esters
can be assessed by thin layer chromatography, gas chromatography (GC), or
liquid
1o chromatography (LC). LC is particularly useful.
Steryl EsteY Compositions
Compositions of the invention include 1 to 75 weight percent (wt %) of a
steryl
ester, 0.3 to 15 wt % of a stabilizer, and 0 to 98.7 wt % of a liquid (e.g.,
water or milk),
~ 5 with the total wt % of a composition being 100. Ingredients within the
compositions
generally are considered food grade, generally recognized as safe (GRAS),
and/or are
U.S. Food and Drug Administration (FDA)-cleared. Typically, steryl esters are
present in
an amount that will provide at least 0.65 g of steryl esters per serving in
the end product.
As used herein, "stabilizer" refers to either a protein or a lipophilic
starch. Suitable
2o proteins are water soluble or dispersible. Caseinates, including the
sodium, potassium,
and calcium salts, are particularly useful. Other proteins, including other
mills protein
sources (e.g., non-fat milk solids or whey solids), soy protein, rice protein,
wheat protein,
oat protein, and mixtures also can be used (see, for example, U.S. Patent No
6,287,616).
Protein hydrolysates (e.g., hydrolyzed soy or whey protein concentrates) also
can be used.
25 See U.S. Patent No. 5,024,849. Generally, protein stabilizers are present
at 0.3 to 10 wt
of the composition (e.g., 1 to 5 or 2 to 3 wt %).
Lipophilic starch refers to modified starch having both hydrophilic and
hydrophobic substituents to give emulsion-stabilizing properties. Suitable
lipophilic
starches include starch alkenyl succinates, which are produced by treating
starch with
3o alkenyl succinic anhydride under controlled pH conditions. Octenylsuccinate
anhydride
starch (OSAN/n-OSAN), which has a hydrophilic carboxyl group and a hydrophobic
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alkene chain, is particularly useful. OSAN/n-OSAN is available from Cargill,
Tnc.
(EmCap Instant 12633) and National Starch (Purity Gum B.E., and N-creamer 46).
Typically, lipophilic starch is present at about 0.3 to 15 wt % of the
composition (e.g., 1 to
3,3.Sto7wt%orStolOwt%).
The term "emulsifier" as used herein means long chain fatty acid esters
including,
but not limited to, distilled monoglycerides, mono- and diglycerides, and
diacetyl tartartic
acid esters of mono- and diglycerides (DATEM). Emulsifiers play an important
role in
formation of the emulsion and also act as dispersion aids in the end
applications. Other
emulsifiers that can be used include polysorbate 60, lecithin and modified
lecithin,
sodium stearyl lactylate, propylene glycol monostearate, succinylated mono-
and
diglycerides, acetylated mono- and diglycerides, propylene glycol mono- and
diesters of
fatty acids, polyglycerol esters of fatty acids, lactylic esters of fatty
acids, glyceryl
monostearate, and mixtures thereof. Emulsifiers can improve emulsification,
stability,
wetting dispersibility, as well as reduce the amount of necessary protein or
Iipophilic
starch. Emulsifiers typically are present at 0.1 to 5 wt % (e.g., 0.1 to 2 wt
%) of the
composition.
In some embodiments, the compositions include a buffer. The term "buffer" as
used herein means an organic or inorganic acid, base, or salt useful to
control pH.
Preferred buffers include, but are not limited to, phosphate buffers such as
dipotassium
2o phosphate, and citrate buffers such as sodium citrate. Buffers may be used
alone or in
combination to achieve desired results of protecting the stabilizer (e.g.,
protein or starch)
against the effects of acid and hard water, which can result in a defect known
as
"feathering." When present, buffers typically are 0.1 to S wt % of the
composition and
more particularly, 0.1 to 1.5 or 1 to 3 wt % of the composition.
Thickeners or hydrocolloids can be added to the composition of the present
invention to contribute extra stabilization, viscosity, and body to the
product. Carageenan
is particularly useful, but other hydrocolloids, including alginates, xanthan
gum, Locust
bean gum, gum arabic, guar gum, cellulose gum, and gum tragacanth, also can be
used.
Thickeners can be present at 0 to 5 wt % (e.g., 0.1 to 0.5 wt % or 0.1 to 0.3
wt %).
3o Sweeteners also can be included in a composition. Sweeteners can be used as
bulking agents (i.e., to provide body or viscosity) or to impart a desired
level of
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sweetness. Corn syrup solids are particularly useful and provide both body and
moderate
sweetness. Maltodextrins also can be used. Sugar or other nutritive sweeteners
such as
liquid corn sweeteners and dextrose can be used if a substantially sweeter
product is
desired. In some embodiments, a sugar substitute such as saccharine,
aspartame,
s acesulfame potassium, or sucrolose can be used in a composition of the
invention.
Bulking agents that do not contribute to sweetness, e.g., starch or cellulose,
also can be
used.
A fat also can be employed in a composition of the present invention. As used
herein, "fat" includes both liquid oils and solid or semi-solid fats. Suitable
fats include
partially or fully hydrogenated vegetable oils; tropical oils such as coconut,
palm, and
palm kernel oil; liquid oils such as soybean, canola, cottonseed, sunflower,
safflower,
corn, and their mid- and high-oleic counterparts; or any combination thereof.
Partially
hydrogenated vegetable oils are particularly useful. A fat can be present at 0
to 74 wt
of a composition of the invention, depending on the end application.
Typically, a fat is
15 present in a liquid composition at 1.5 to 7 wt % or 7 to 13 wt %. In
powdered
compositions, the fat content can range from 20 to 74 wt %. For example, in a
coffee
creamer, the fat content can be 20 to 35 wt %. In a powdered drink mix, the
fat content
can be 35 to SO wt%. ~ther high fat compositions can have fat contents of 55
to 75 wt %.
Although a composition contains fat, the small serving size (for example, 15
mL or less
2o depending on steryl ester concentration) of the composition will have
minimum impact in
the end use (for example, a cup of coffee) and on an overall diet. It has been
observed
that, while not required, including a small portion of partially hydrogenated
vegetable oil
in the composition of the present invention aids in solubility of the steryl
esters, and the
formation and stability of the emulsion.
2s Additional ingredients can be included in compositions, including flavors
(e.g.,
vanilla, hazelnut, Irish creme, mocha, almond, liqueurs, or chocolate);
coloring agents;
antioxidants to increase oxidative stability (e.g., ethoxyquin, vitamin E,
butylated
hydroxyanisole (BHA), butylated hydroxytoluene (BHT), tertiary
butylhydroquinone
(TBHQ), or ascorbyl palmitate); and flow agents (to prevent caking and
clumping in dry
so products) such as sodium aluminosilicate or silicon dioxide.
to
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Preparation of Steryl Ester Compositions
Compositions of the invention can be prepared by mixing and heating the steryl
esters, the emulsifiers, and, optionally, a fat (e.g., a vegetable oil) to
obtain a melt.
Typically, the melt can be obtained by heating the components, with stirring,
to
approximately 1SS°F. The speed at which the melt is obtained can be
accelerated by
elevating the temperature. A skilled artisan will appreciate that the
temperature required
will vary depending upon the specific steryl esters and emulsifiers utilized.
The aqueous phase can be prepared by dissolving a buffer and stabilizer (i.e.,
protein or lipophilic starch) in water and heating the solution to a
temperature close to
1 o that of the steryl esterlemulsifier melt. The aqueous phase then can be
slowly added to
the melt while blending with high shear to obtain an emulsion. Additional
desired
components (e.g., bulking agents, flavorings, fats, coloring agents, flow
agents, or
antioxidants) can be added with mixing to obtain a uniform mixture. The
mixture then
can be pasteurized or otherwise heat processed using known techniques. To
reduce
~5 particle size of the fat droplets, a two-stage homogenization can be done
(e.g., at 2500 psi
and 500 psi). The resulting homogenized product can be packaged to produce a
liquid
premix or spray dried to produce a powdered premix product. The powdered form
may
be agglomerated to instantize the product and improve dispersibility when it
is stirred into
the aqueous end application.
2o Formulating Compositions of the Invention
Compositions of the invention can be liquids, gels, or powders, and can be
formulated such that the steryl esters are either dilute or concentrated,
depending on the
desired end use. Typically, liquid compositions of the invention include from
1 to 40 wt
of a steryl ester, 0.3 to 15 wt % of a stabilizer, 0.1 to S wt % of an
emulsifier, and from
25 20 to 98.6 wt % of a liquid. For example, a liquid composition containing a
relatively
low amount of steryl esters can include 1 to 10 wt % of a steryl ester, O.S to
l.S wt % of a
stabilizer (e.g., a caseinate such as sodium caseinate), 0.2 to 0.6 wt % of an
emulsifier
(e.g., mono- and diglycerides and/or diacetyl tartartic acid esters thereof);
0.1 to l.S wt
of a buffer (e.g., dipotassium phosphate), 0.5 to 1S wt % of a bulking agent
(e.g., corn
3o syrup solids); 3 to ZO wt % of a fat (e.g., partially hydrogenated
vegetable oil), and 40 to
11
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80 wt % of a liquid (e.g., water). Such a composition is a stable emulsion
that is fluid and
easily dispersible and can be used as a creamer for tea or coffee. Such
compositions
further can include sweetener and flavorings. For example, 2S to 30 wt % of a
sweetener
(e.g., sugar), and 0.1 to 2 wt % of a flavoring (e.g., French vanilla) can be
added.
s In other embodiments, a liquid composition can be used as a beverage premix
emulsion and contain a more concentrated amount of steryl esters. For example,
a liquid
composition can include 1 S to 2S wt % of a steryl ester, O.S to 8 wt % of a
stabilizer (e.g.,
a caseinate such as sodium caseinate or a lipophilic starch), 0.2 to 1 wt % of
an emulsifier
(e.g., mono- and diglycerides and/or diacetyl tartartic acid esters thereof);
0.1 to 1.S wt
0 of a buffer (e.g., dipotassium phosphate), O.S to 3S wt % of a bulking agent
(e.g., corn
syrup solids); 0 to 4 wt % of a fat (e.g., partially hydrogenated vegetable
oil), and 3S to 80
wt % of a liquid (e.g., water).
In other embodiments, the composition can be dry (e.g., powdered) and include
1
to 7S wt % of a steryl ester and 0 to S wt % of a liquid. It is noted that
"dry" material
15 may contain residual levels of liquid. Powdered forms of the composition
can be used in
powdered drink mixes with relatively larger serving sizes (e.g., cappuccino
mix or hot
chocolate rnix). For example, a powdered composition can include about S to 1S
wt % of
a steryl ester, 1 to S wt % of a stabilizer (e.g., a caseinate such as sodium
caseinate), 0.3
to 1.S wt % of an emulsifier (e.g., mono- and diglycerides andlor diacetyl
tartartic acid
2o esters thereofj, 1 to 3 wt % of a buffer (e.g., dipotassium phosphate), 70
to 80 wt % of a
bulking agent (e.g., corn syrup solids), and S to 10 wt % of a fat (e.g.,
partially
hydrogenated vegetable oil). See, for example, the compositions of Examples 6
and 7. In
such a composition, the water for the oil-in-water emulsion is provided by the
water in
which the buffer and stabilizer are dissolved or dispersed.
25 Compositions containing a higher concentration of steryl esters can be
produced
by concentrating a liquid composition using evaporative or drying techniques
such as
spray drying drum-drying, or tray drying, or any combination thereof. As a
result, the
amount of liquid in the composition can be reduced to a desired end point. In
some
embodiments, it may be desirable to produce compositions having a gel-like
consistency
3o and a liquid content of about S to 20 wt %.
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In other embodiments, it may be desired to produce powdered compositions. For
example, a liquid composition containing 20 to 23 wt % of steryl esters, 0.5
to 7 wt % of
a stabilizer (e.g., 0.5 to 2 wt % of a protein such as sodium caseinate or 4
to 7 wt % of a
lipophilic starch), 0.3 to 1 wt % of an emulsifier, 1 to 2 wt % of a buffer, 3
to 40 wt % of
a bulking agent (e.g., corn syrup solids), 0 to 10 wt % of a fat, and 35 to 45
wt % of a
liquid (e.g., water), can be spray dried to obtain an easily dispersible
powder. After
drying, such compositions contain approximately 30 to 35 wt % of steryl
esters. See, for
example, the compositions of Examples 3, 5, and 8-10. When such compositions
contain
a lipophilic starch, it is particularly useful for adding to orange juice,
powdered fruit
drinks such as Crystal Light~, or other acidic beverages to provide the
desired serving of
steryl esters.
Compositions of the invention can be incorporated into a variety of food or
beverages. For example, liquid or powdered compositions can be added to coffee
and tea
beverages (i.e., as a coffee creamer), as well as milk, yogurt and yogurt
drinks, cocoa,
instant breakfast drinks, soy drinks, juice drinks and smoothies, and meal
replacement
beverages. As described herein, a water dispersible steryl ester composition
of the
invention containing 35 wt % of steryl esters had superior whitening
properties than a
commercially available non-dairy creamer product. In addition, compositions
can be
added to milk or another liquid that is subsequently used in the preparation
of another
2o food such as breakfast cereal (e.g., instant oatmeal), scrambled egg
whites, mashed
potatoes, or pudding. Compositions also can be used in the preparation of
soups, sauces,
dressings, mousse, desserts, and toppings. Formulations can be assessed for
palatability
and mouthfeel using a panel of trained taste testers according to known
techniques.
The amount of steryl ester composition that is incorporated into the product
(e.g.,
25 powdered drink mix, liquid coffee creamer, or beverage premix emulsion)
will depend on
the end use and the desired concentration of steryl esters in the product.
Typically, steryl
ester compositions of the invention represent 0.5 to 60 wt % (e.g., 1 to 40 wt
%) of the
end product. For example, as described in Example 7, a low fat instant
cappuccino mix
can be produced that will deliver 0.65 g of steryl esters per serving. Such a
mix typically
so contains 50 to 60 wt % sugar, 25 to 35 wt % of a dilute steryl ester
composition of the
invention, 10 to 15 wt % nonfat dry milk, 1 to 2 wt % instant coffee,
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carboxymethylcellulose (CMC) 0.1 to 1 wt %, 0.1 to 1 wt % of a flow agent, 0.1
to 0.75
wt % salt, and 0.1 to I.0 wt % of a flavoring agent. Steryl ester compositions
stabilized
by a lipophilic starch can be stirred into a powdered low calorie fruit drink
mix to provide
the desired serving of steryl esters. See Example 9.
s The invention will be further described in the following examples, which
does not
limit the scope of the invention described in the claims.
EXAMPLES
Example 1 - Unsweetened Steryl Ester Premix for delivering 0.65g steryl
o esters per lSmL serving.
An unsweetened steryl ester premix was prepared using the ingredients listed
in
Table 1.
TABLE 1
Ingredient % (hy weight)
Steryl Esters (Cargill Incorporated) 5.00
Partially Hydrogenated Soybean OiI (Cargill5.00
5700,1V= )
Distilled Monoglycerides (Danisco DIMODAN0.20
OK)
DATEM (Danisco PANODAN FDPK) 0.20
Water 78.35
Dipotassium Phosphate (Astaris) 0.20
Sodium Caseinate (New Zealand Milk Products1.00
Alanate 110)
Carageenan (Danisco CL220) 0.10
25 DE Corn Syrup Solids (Cerestar Dry 10.00
MD 01915)
Total 100.00
Ts Procedure:
1. The steryl esters, soybean oil, and emulsifiers (distilled monoglycerides
and DATEM) were combined and heated with mixing to 155°F.
2. Dipotassium phosphate was dissolved in the water and heated to
120°F.
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3. The sodium caseinate and carrageenan were pre-mixed then slowly added
to the dipotassium phosphate solution with mixing to prevent clumping. The
mixture was
heated to 150°F and held for 10 minutes while mixing to achieve
complete solubilization.
4. The water phase from step 3 was slowly poured into the steryl ester phase
while blending with high shear to form an emulsion.
5. Corn syrup solids were gradually added to the emulsion with vigorous
mixing until a uniform mixture was obtained.
6. The mixture was batch pasteurized at 165°F for 15 minutes.
7. The pasteurized mixture was homogenized in a two-stage process at 2500
o psi and 500 psi.
The resulting product was a very fluid, bland tasting, stable emulsion that
was
easily dispersible.
Example 2 - Concentrated, Unsweetened Steryl Ester Premix
~5 A concentrated unsweetened steryl ester premix was prepared using the
ingredients listed in Table 2. The premix was prepared as described in steps 1
to 5 of
Example 1. This formula yields a slightly thicker, smooth, flowable, stable
emulsion that
was easily dispersible. Approximately 3.Sg of premix delivers 0.658 steryl
esters.
TABLE 2
In redient o
g /o (by weight)
Steryl Esters (Cargill) 19.00
Partially Hydrogenated Soybean Oil (Cargill 5700, IV= ) 2.50
Distilled Monoglycerides (Danisco D1MODAN OIL) 0.20
DATEM (Danisco PANODAN FDPI~) 0.20
Water 74.55
Dipotassium Phosphate (Astaris) 1.20
Sodium Caseinate (New Zealand Milk Products1.00
Alanate 110)
Carageenan (Danisco CL220) 0.05
25 DE Corn Syrup Solids (Cerestar Dry MD 1.00
01915)
Total 100.00
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Example 3 - Unsweetened Powdered Steryl Ester Premix.
An unsweetened powdered steryl ester premix was prepared by following steps 1
through 5 of Example 1. The mixture then was homogenized in a two-stage
process at
3000 psi and 500 psi. The emulsion was spray dried using standard techniques
to produce
a fine, white, easily dispersible powder.
TABLE 3
Tngredient % (by weight)
Steryl Esters (Cargill) 21.00
Distilled Monoglycerides (Danisco DIMODAN0.20
OK)
DATEM (Danisco PANODAN FDPK) 0.20
Water 40.10
Dipotassium Phosphate (Astaris) 1.20
Sodium Caseinate (New Zealand Milk Products1.80
Alanate 110)
25 DE Corn Syrup Solids (Cerestar Dry 35.50
MD 01915)
Total 100.00
Example 4 - Sweetened and Flavored Steryl Ester Premix:
A sweetened and flavored steryl ester premix was prepared using the
ingredients
in Table 4.
TABLE 4
Ingredient % (by weight)
Partially Hydrogenated Soybean Oil (Cargill8.75
5700, IV= )
Steryl Esters (Cargill) 4.70
Distilled Monoglycerides (Danisco DIMODAN0.20
OK)
DATEM (Danisco PANODAN FDPK) 0.20
Water 49.847
Dipotassium Phosphate (Astaris) 1.20
Sodium Caseinate (New Zealand Milk Products1.00
Alanate 110)
Carageenan (Danisco CL220) 0.10
25 DE Corn Syrup Solids (Cerestar Dry 3.00
MD 01915)
Sugar 30.00
Salt 0.003
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Ingredient % (by weight)
French Vanilla Flavoring 1.00
Total 100.00
Procedure:
1. The steryl esters, soybean oil, and emulsifiers (distilled monoglycerides
aald DATEM) were combined with mixing and heated to 155°F to form a
melt.
2. Dipotassium phosphate was dissolved in water and heated to 120°R
3. The sodium caseinate, carrageenan, sugar, and salt were premixed and
slowly added to the dipotassium phosphate solution with mixing to prevent
clumping.
The resulting aqueous phase was heated to 150°F and held for 10 minutes
while mixing to
solubilize.
4. The water phase was slowly poured into the steryl ester phase while
stirring to form an emulsion.
5. The flavoring and corn syrup solids were gradually added to the emulsion
with vigorous mixing until a uniform mixture was obtained.
6. The formulation was blended in a blender with high shear for 1 minute.
15 This product was a very fluid, sweet vanilla tasting, stable emulsion that
was
easily dispersible.
Example 5 - Coffee sweetened, whitened, and fortified with a steryl ester
premix.
2o A 15 mL serving of a liquid steryl ester premix (as described in Examples 1
and 4)
was poured into a freshly brewed cup (6 oz, 180 mL) of hot coffee and stirred
with a
spoon to disperse. The result was a very pleasant tasting, whitened coffee
with creamy
mouthfeel, reduced bitterness, and a healthful dose of steryl esters (0.65g).
The creamer
remained dispersed in the coffee for over an hour (until the coffee had cooled
to room
2s temperature) with no apparent feathering or oiling out.
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Example 6 - Water Dispersible Steryl Ester for Powdered Drink Mix
Applications.
In this example, steryl esters are used in combination with partially
hydrogenated
vegetable oil (9.00% and 7.76%, respectively) to produce a water dispersible
powder that
s can be used in powdered drink mixes such instant cappuccino.
TABLE 5
Ingredient % (by weight)
Dipotassium Phosphate 2.00
Sodium Caseinate 3.00
Corn Syrup Solids 77.21
Steryl Esters 9.00
Partially Hydrogenated Vegetable7,7(,
Oil
Mono- and Diglycerides 0.70
DATEM 0.33
Total 100.00
Procedure:
1. The steryl ester, vegetable oil, and emulsif ers (mono- and diglycerides
and
DATEM) are combined together and are heated with mixing to 155°F.
2. The dipotassium phosphate is dissolved in the water and is heated to
120°F.
3. The caseinate is slowly added to the dipotassium phosphate solution with
~ 5 mixing. Heat to 150°F and hold for 10 minutes for complete
solubilization.
4. The water phase from step 3 is slowly poured into the steryl ester phase
while blending with high shear to form an emulsion.
5. The corn syrup solids are gradually added to the emulsion with mixing
until dissolved.
6. The emulsion is batch pasteurized at 165°F for 15 minutes.
7. The pasteurized emulsion is homogenized in a two-stage process at
2500/500 psi.
1s
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8. The homogenized emulsion is spray dried with an inlet temperature of
400°F and outlet temperature of 200°ft
Example'? - Low Fat Instant Cappuccino Mix Containing Water Dispersible
s Steryl Esters.
A low fat instant cappuccino mix is prepared by dry blending all ingredients
listed
in the following Table. The mix, which contains 29% water dispersible steryl
esters, will
deliver 0.658 of steryl esters per serving. To make a cup of cappuccino, add 6
oz (180 g)
of hot water to 25 g of cappuccino mix and stir.
TABLE 6
Ingredient % (by weight)
Sugar 56.50
Water Dispersible Steryl Esters (9% steryl esters) 29.00
Nonfat Dry Milk 11.00
Instant Coffee 1.50
CMC, high VlSCOSlty 0.50
Salt 0.50
Flavor 0.50
Flow Agent 0.50
Total 100.00
Example 8 - Water dispersible steryl ester composition for powdered drink
mix applications:
A water dispersible steryl ester composition was made using the ingredients in
Table 7. Tn this formulation, lipophilic starch was used in place of sodium
caseinate. The
spray-dried product contained 35 wt % of steryl esters. This product is
relatively
concentrated and particularly useful in applications with a small serving
size. The starch
stabilizer shows improved acid stability.
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TABLE 7
Ingredient % (by weight)
Water 40.10
Potassium Diphosphate 1.20
EmCap Instant 12633 Lipophilic5.60
Starch
25 DE Corn Syrup Solids 31.35
Steryl Esters 21.00
Monoglycerides 0.50
DATEM 0.25
Total 100.00
Procedure:
1. Steryl esters and emulsifiers were combined together with mixing and
heated to 155°F.
2. Dipotassium phosphate was dissolved in the water and heated to
120°F.
3. The starch was slowly added to the dipotassium phosphate solution with
mixing to form the water phase.
4. The water phase was slowly poured into the steryl ester phase while
o blending with high shear to form an emulsion.
5. The corn syrup solids were gradually added to the emulsion with mixing
until dissolved.
6. The emulsion was pasteurized at 165°F for 15 minutes.
7. The emulsion was homogenized in a two-stage process at 2500/500 psi.
8. The homogenized emulsion was spray dried with an inlet temperature of
400°F and an outlet temperature of 200°F.
Example 9: Low Calorie Powdered Fruit Drink Containing Water
Dispersible Steryl Esters
2o The following product contains 40% of the composition described in Example
8
and will deliver 0.658 steryl esters per serving. To make a glass of fruit
drink, add ~ oz
(240 g) of cold water to 5 g of the fruit drink powder and stir.
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TABLE 8
Ingredient % (by weight)
Powdered low calorie fruit drink 60.0
Water Dispersible Steryl Esters 40,0
Total 100.0
Example 10: Orange Juice Supplemented with Water Dispersible Steryl
Esters
The following formula describes use of the composition of Example 8 in an
orange juice application. The formula contains 0.65g steryl esters per 8 oz
(240 g)
serving of juice. The lipophilic starch stabilized form of the invention can
be easily
stirred into a cold, acidic beverage and disperses well. To make a glass of
steryl ester
fortified orange juice, add 1 teaspoon (2 g) of water dispersible steryl
esters (e.g., from
o Example 8) to an 8 oz glass of orange juice and stir.
TABLE 9
Ingredient % (by weight)
Single Strength (ready to drink) Orange Juice 99.1
Water Dispersible Steryl Esters 0.9
Total 100.0
OTHER EMBODIMENTS
The above specification, examples and data provide a complete description of
the
s manufacture and use of the product of the invention. Since many embodiments
of the
invention can be made without departing from the spirit and scope of the
invention, the
invention resides in the claims hereinafter appended.
21
